+SHIP’s Board of Directors is composed of a diverse cross-section of individuals who have collectively harnessed their passion for children, experience, and skills to help steer SHIP to become a leading youth development and support nonprofit agency. This team have agreed to lead SHIP as we set our goals, build our plans, and establish our internal systems. Their diverse expertise and experience provide a strong foundation for SHIP’s continual growth and maturity as a nonprofit organization. The Board of Directors works closely with SHIP’s staff to make progress toward the organization’s mission.
Executive Committee
Andi Overton, President
Kim Whitely, Vice President
Kim brings more than 20 years of staffing industry and search experience to MeeDerby. She leads the day-to-day operations of MeeDerby, supporting the team in placing managers and executives in the staffing industry. Kim is active with the American Staffing Association (ASA), participating in the Women in Leadership Council, the Mentor/Mentee Program, former Chair of the Direct Hire Council and a 2023 advisor to the Women’s Business Collaborative’s (WBC) Staffing Workstream. Kim is active in her community as a board member with SHIP (Student Homeless Initiative Partnership), is a volunteer dive coach for her son’s highschool and a committee member of BoyScout Troop 278. Before joining MeeDerby, Kim spent 15 years with Spherion in leadership and revenue-driving roles across multiple staffing verticals.
Caroline Orlowski, Treasurer
Caroline Orlowski works as a Managing Director at Cottonwood Ag Partners. Over the past 15 years, she has volunteered for several different organizations, which have instilled a passion in her for helping homeless youths and led her to serve on SHIP’s board. She values how SHIP both helps youths in their current situation and works to set them up for future success. She lives on a farm in Frederick County with her husband and two children.
Directors
Stephanie Fisher
Stephanie Fisher is a Project Engineer at CAS Engineering, where she works in single-family residential development projects. Scholarships and access to education have played a significant role in her own life, inspiring a deep commitment to supporting students and educational initiatives since graduating college. Stephanie has been involved with a variety of education-focused nonprofits and is passionate about creating pathways to opportunity for young people. Serving on the SHIP Board is especially meaningful to her as it allows her to make a direct impact in her local community. A Frederick County resident, mom of four, volunteer, and Rotarian, Stephanie wholeheartedly believes in SHIP’s mission to support students facing housing insecurity and help set them up for long-term success.
Kylie McCleaf
Kylie is currently the COO at JSSA, a large non-profit that serves the National Capital area. She is skilled in Risk Management, Human Resources, Financial Management, Public Speaking, Corporate Compliance, Donor and Volunteer Relationships, and Business Development. She is a graduate of Leadership Fairfax Institute, Class of 2022. In 2015, Kylie was selected as a recipient of Washington SmartCEO’s prestigious 2015 BRAVA! Award, which celebrates the achievements of 40 Greater Washington’s top women business leaders. She is married with 3 children and resides in Frederick County, Md.
Jesica Roman
Jesica Roman is a Frederick County resident and local professional who lives and works in the community. Originally from Gaithersburg, she moved to Frederick County with her family and is active locally both personally and professionally. She holds a Bachelor of Science degree in psychology and has worked in real estate since 2006; Jesica was also the executive director of a Montgomery County nonprofit for four years. Jesica focuses on serving her clients throughout Maryland while also engaging in community service with various local non-profits. Jesica is a member of the board of directors for SHIP of Frederick County. Her role on the board reflects her commitment to community service and advocacy for vulnerable local students and youth. Having children of her own in FCPS, she recognizes the importance of education for all and the role it plays in the cycle of poverty. Students with housing insecurity face many challenges that SHIP addresses, and as part of the board Jesica can be an active participant in the solution.
Dana Adams Tate
Dana Adams Tate is a development professional in higher education. In her career, she is dedicated to education accessibility and building relationships that inspire philanthropy to support students. This commitment extends to her volunteer service on the SHIP Board, where she helps advance efforts to support Frederick County students who are facing homelessness and housing insecurity. Having grown up relying on government and community assistance, she brings a personal understanding of the need to provide young people with the services, resources, and pathways necessary for success.
Jim Racheff, Immediate Past President (Non-voting)
